CN111995564B - Organic compound, electronic element, and electronic device - Google Patents

Organic compound, electronic element, and electronic device Download PDF

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CN111995564B
CN111995564B CN202010807416.XA CN202010807416A CN111995564B CN 111995564 B CN111995564 B CN 111995564B CN 202010807416 A CN202010807416 A CN 202010807416A CN 111995564 B CN111995564 B CN 111995564B
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ring
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CN111995564A (en
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马天天
杨雷
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Abstract

The application belongs to the technical field of organic materials, and provides an organic compound, an electronic element and an electronic device shown in chemical formulas 1 and 2. The organic compound, in which two of chemical formula 2 are combined with any adjacent two of four of chemical formula 1 to form a condensed ring, can improve electron transport properties of the electronic component.
Figure DDA0002629645200000011

Description

Organic compound, electronic element, and electronic device
Technical Field
The present disclosure relates to the field of organic materials, and more particularly, to an organic compound, an electronic component, and an electronic device.
Background
Organic electroluminescent materials (OLEDs), as a new generation display technology, have the advantages of being ultra-thin, self-luminescent, wide viewing angle, fast response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, low energy consumption, and the like, and have been widely used in the industries of flat panel display, flexible display, solid state lighting, vehicle-mounted display, and the like.
An organic light emitting device generally includes an anode, a cathode, and an organic material layer therebetween. The organic material layer is generally formed in a multi-layered structure composed of different materials to improve the luminance, efficiency and lifetime of the organic electroluminescent device, and may be composed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the organic light emitting device structure, when a voltage is applied between two electrodes, holes and electrons are injected from an anode and a cathode into an organic material layer, respectively, excitons are formed when the injected holes and electrons meet, and light is emitted when the excitons return to a ground state.
In the conventional organic electroluminescent device, the most important problems are lifetime and efficiency, and as the display has been increased in area, the driving voltage has been increased, and the luminous efficiency and the power efficiency have been increased, so that it is necessary to continuously develop new materials to further improve the performance of the organic electroluminescent device.
The above information disclosed in this background section is only for enhancement of understanding of the background of the application and therefore it may contain information that does not constitute prior art that is known to a person of ordinary skill in the art.
Disclosure of Invention
An object of the present application is to provide an organic compound, an electronic element, and an electronic device to improve the performance of an organic electroluminescent device.
In order to achieve the purpose of the invention, the following technical scheme is adopted in the application:
according to a first aspect of the present application, there is provided an organic compound having a structural formula as shown in chemical formula 1 and chemical formula 2:
Figure BDA0002629645180000011
wherein two of chemical formula 2 are combined with any adjacent two of four of chemical formula 1 to form a fused ring;
the ring B is a benzene ring or a condensed aromatic ring with 10-14 ring carbon atoms;
l is selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms;
r is selected from substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms and substituted or unsubstituted cycloalkyl with 3-20 carbon atoms;
R1、R2、R3the same or different, and are respectively and independently selected from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms, and substituted or unsubstituted cycloalkyl with 3-20 carbon atoms;
ntis a substituent RtT is any integer of 1-3; when t is 1, ntSelected from 1,2, 3 or 4; when t is selected from 2, ntIs selected from 1 or 2; when t is 3, ntSelected from 1,2, 3,4, 5, 6, 7 or 8; when in usentWhen greater than 1, any two RtThe same or different.
According to a second aspect of the present application, there is provided an electronic component comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the organic compound described above.
According to a third aspect of the present application, an electronic device is provided, which includes the above electronic component.
Drawings
The above and other features and advantages of the present application will become more apparent by describing in detail exemplary embodiments thereof with reference to the attached drawings.
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
Fig. 3 is a nuclear magnetic spectrum of compound 28 according to one embodiment of the present application.
The reference numerals of the main elements in the figures are explained as follows:
an anode 100; a hole injection layer 310; a hole transport layer 321; an electron blocking layer 322; an organic electroluminescent layer 330; a hole blocking layer 340; an electron transport layer 350; an electron injection layer 360; a cathode 200; an electronic device 400.
Detailed Description
Example embodiments will now be described more fully with reference to the accompanying drawings. Example embodiments may, however, be embodied in many different forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of example embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the application.
In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals denote the same or similar structures in the drawings, and thus detailed descriptions thereof will be omitted.
An organic compound according to an embodiment of the present application is characterized in that the structural formula of the organic compound is shown in chemical formula 1 and chemical formula 2:
Figure BDA0002629645180000021
wherein two of chemical formula 2 are combined with any adjacent two of four of chemical formula 1 to form a fused ring;
the ring B is a benzene ring or a condensed aromatic ring with 10-14 ring carbon atoms;
l is selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms;
r is selected from substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms and substituted or unsubstituted cycloalkyl with 3-20 carbon atoms;
R1、R2、R3the same or different, and are respectively and independently selected from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms, and substituted or unsubstituted cycloalkyl with 3-20 carbon atoms;
ntis a substituent RtT is any integer of 1-3; when t is 1, ntSelected from 1,2, 3 or 4; when t is selected from 2, ntIs selected from 1 or 2; when t is 3, ntSelected from 1,2, 3,4, 5, 6, 7 or 8; when n istWhen greater than 1, any two RtThe same or different.
In this application, a group is unsubstituted if it is not specified to be substituted.
In the present application, the description that "… … is independently" and "… … is independently" and "… … is independently selected from" is used interchangeably and should be understood broadly to mean that the particular items expressed between the same symbols in different groups do not affect each other, or that the particular items expressed between the same symbols in the same groups do not affect each other. For example,') "
Figure BDA0002629645180000031
Wherein each q is independently 0, 1,2 or 3, each R "is independently selected from hydrogen, deuterium, fluoro, chloro" and has the meaning: the formula Q-1 represents that Q substituent groups R ' are arranged on a benzene ring, each R ' can be the same or different, and the options of each R ' are not influenced mutually; the formula Q-2 represents that each benzene ring of biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on the two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced with each other.
In the present application, the term "substituted or unsubstituted" means that a functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group or an unsubstituted aryl group having a substituent Rc. Wherein Rc as the substituent may be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 30 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, a cycloalkenyl group having 5 to 10 carbon atoms, a heterocycloalkenyl group having 4 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, an arylthio group having 6 to 18 carbon atoms, Phosphorus oxy group with 6-18 carbon atoms, alkyl sulfonyl group with 6-18 carbon atoms, trialkyl phosphino group with 3-18 carbon atoms and trialkyl boron group with 3-18 carbon atoms.
The connection of chemical formula 2 to the different positions of chemical formula 1 may form different structures. Specifically, the organic compound of the present application may have any one of the following chemical formulas a, B, C, D, E, and F:
Figure BDA0002629645180000032
Figure BDA0002629645180000041
the core structure of the application is a planar structure which is formed by fusing an adamantane screwed fluorenyl and indole and has high rigidity, fast hole mobility and high first triplet state energy level; an electron-rich/electron-deficient aryl or heteroaryl is introduced to the indole nitrogen atom modification mode, so that a molecular structure suitable for a light-emitting layer main body material in an organic electroluminescent material can be formed; when the material is applied to a single-component bipolar host or one of two-component mixed host materials, the efficiency and the service life of the organic electroluminescent device can be enhanced; particularly, when the adamantane is combined with the condensed plane structure in a screwing mode, the intermolecular stacking can be effectively reduced, so that the crystallization performance of the material is reduced, and the service life of the device is further prolonged.
In the present application, ring B, L, R, R1、R2、R3The number of carbon atoms of (b) means all the number of carbon atoms. For example, if L is selected from substituted arylene having 10 carbon atoms, then all of the carbon atoms of the arylene and substituents thereon are 10; if ring B is selected from substituted aryl groups having 10 carbon atoms, then all carbon atoms of the aryl group and substituents thereon are 10.
In the present application, when a specific definition is not otherwise provided, "hetero" means that at least 1 hetero atom of B, N, O, S, Si, Se, or P, etc. is included in one functional group and the remaining atoms are carbon and hydrogen. An unsubstituted alkyl group can be a "saturated alkyl group" without any double or triple bonds.
In the present application, "alkyl" may include straight chain alkyl or branched alkyl. Alkyl groups may have 1 to 20 carbon atoms, and numerical ranges such as "1 to 20" refer herein to each integer in the given range; for example, "1 to 20 carbon atoms" refers to an alkyl group that may contain 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 carbon atoms, 12 carbon atoms, 13 carbon atoms, 14 carbon atoms, 15 carbon atoms, 16 carbon atoms, 17 carbon atoms, 18 carbon atoms, 19 carbon atoms, or 20 carbon atoms. The alkyl group can also be a medium size alkyl group having 1 to 10 carbon atoms. The alkyl group may also be a lower alkyl group having 1 to 6 carbon atoms. Further, the alkyl group may be a substituted or unsubstituted alkyl group of 1 to 5. Specific examples of the alkyl group having 1 to 5 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl and the like.
In the present application, "alkenyl" refers to a hydrocarbon group comprising one or more double bonds in a straight or branched hydrocarbon chain. Alkenyl groups may be unsubstituted or substituted. An alkenyl group may have 2 to 6 carbon atoms, and whenever appearing herein, numerical ranges such as "2 to 6" refer to each integer in the given range; for example, "2 to 6 carbon atoms" means that 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms can be included. For example, the alkenyl group may be a vinyl group.
In the present application, cycloalkyl refers to a saturated hydrocarbon containing an alicyclic structure, including monocyclic and fused ring structures. Cycloalkyl groups may have 3-10 carbon atoms, a numerical range such as "3 to 10" refers to each integer in the given range; for example, "3 to 10 carbon atoms" refers to a cycloalkyl group that may contain 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, or 10 carbon atoms. The cycloalkyl group may be a small ring, a normal ring or a large ring having 3 to 10 carbon atoms. Cycloalkyl groups can also be divided into monocyclic-only one ring, bicyclic-two rings-or polycyclic-three or more rings. Cycloalkyl groups can also be divided into spiro rings, fused rings, and bridged rings, in which two rings share a common carbon atom, and more than two rings share a common carbon atom. In addition, cycloalkyl groups may be substituted or unsubstituted.
In the present application, aryl refers to an optional functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups connected by carbon-carbon bond conjugation, a monocyclic aryl group and a fused ring aryl group connected by carbon-carbon bond conjugation, two or more fused ring aryl groups connected by carbon-carbon bond conjugation. That is, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered as an aryl group in the present application. Wherein the aryl group does not contain a hetero atom such as B, N, O, S, Se, Si or P. For example, biphenyl, terphenyl, and the like are aryl groups in this application. Examples of the aryl group may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, hexabiphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl, phenanthrenyl, pyrenyl,
Figure BDA0002629645180000053
and the like, without limitation.
In this application, substituted aryl refers to an aryl group in which one or more hydrogen atoms are replaced with another group. For example, at least one hydrogen atom is substituted with deuterium atoms, F, Cl, I, CN, hydroxyl, amino, branched alkyl, straight chain alkyl, cycloalkyl, alkoxy, alkylamino, alkylthio, or other groups. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothiophene-substituted phenyl, pyridine-substituted phenyl, and the like. Specific examples of aryl-substituted aryl groups include, but are not limited to, phenyl-substituted naphthyl, phenyl-substituted phenanthryl, naphthyl-substituted phenyl, phenyl-substituted anthracyl, and the like. It is understood that the number of carbon atoms of the substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, a substituted aryl group having 20 carbon atoms means that the total number of carbon atoms of the aryl group and the substituent on the aryl group is 20. For example, 9, 9-dimethylfluorenyl is a substituted aryl group having 15 carbon atoms.
In the present application, the heteroaryl group may be a heteroaryl group including at least one of B, O, N, P, Si, Se, and S as a heteroatom. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds in a conjugated manner, and any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Exemplary heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuryl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzosilyl, dibenzofuryl, phenyl-substituted dibenzofuryl, Dibenzofuranyl-substituted phenyl groups, and the like, without being limited thereto. Wherein, thienyl, furyl, phenanthroline group and the like are heteroaryl of a single aromatic ring system, and N-aryl carbazolyl, N-heteroaryl carbazolyl, phenyl-substituted dibenzofuryl group and the like are heteroaryl of a plurality of aromatic ring systems connected by carbon-carbon bond conjugation.
In this application, the explanation for aryl applies to arylene, the explanation for heteroaryl applies equally to heteroarylene, the explanation for alkyl applies to alkylene, and the explanation for cycloalkyl applies to cycloalkylene.
In this application, the ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6-membered aryl. The 6-to 10-membered aromatic ring means a benzene ring, an indene ring, a naphthalene ring and the like.
An delocalized bond in the present application refers to a single bond extending from a ring system
Figure BDA0002629645180000051
It means that one end of the linkage may be attached to any position in the ring system through which the linkage extends, and the other end to the rest of the compound molecule.
For example, as shown in the following formula (f), naphthyl represented by the formula (f) is connected with other positions of the molecule through two non-positioned connecting bonds penetrating through a double ring, and the meaning of the naphthyl represented by the formula (f-1) comprises any possible connecting mode shown in the formula (f-10).
Figure BDA0002629645180000052
Figure BDA0002629645180000061
As another example, in the following formula (X '), the phenanthryl group represented by formula (X') is bonded to the rest of the molecule via an delocalized bond extending from the middle of the phenyl ring on one side, and the meaning of the phenanthryl group includes any of the possible bonding modes shown in formulas (X '-1) to (X' -4).
Figure BDA0002629645180000062
An delocalized substituent, as used herein, refers to a substituent attached by a single bond extending from the center of the ring system, meaning that the substituent may be attached at any possible position in the ring system. For example, in the following formula (Y), the substituent R group represented by the formula (Y) is bonded to the quinoline ring via an delocalized bond, and the meaning thereof includes any of the possible bonding modes shown by the formulas (Y-1) to (Y-7).
Figure BDA0002629645180000063
The meaning of the connection or substitution is the same as that of the connection or substitution, and will not be described further.
In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, iodine.
In the present application, specific examples of the trialkylsilyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, and the like.
In the present application, specific examples of triarylsilyl groups include, but are not limited to, triphenylsilyl groups, and the like.
A substituent in the L, a substituent in the R, the R1、R2And R3Wherein the substituents are the same or different from each other and are each independently selected from deuterium, fluorine, chlorine, bromine, cyano, alkyl having 1 to 5 carbon atoms, alkenyl having 2 to 6 carbon atoms, haloalkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 12 carbon atoms optionally substituted with 0, 1,2 or 3 substituents selected from deuterium, fluorine, chlorine, bromine, cyano, alkyl, heteroaryl having 6 to 12 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, arylsilyl having 6 to 18 carbon atoms; alternatively, at each L, R, R1、R2And R3When two substituents are present on the same atom, optionally, two of the substituents are attached to each other to form, together with the atom to which they are commonly attached, a 5-to 18-membered aliphatic ring or a 5-to 18-membered aromatic ring.
Alternatively, chemical formula 2 of the present application may have any one of the following chemical formulas 2-1, 2-2, 2-3, and 2-4:
Figure BDA0002629645180000064
specifically, ring B may be a benzene ring or a naphthalene ring.
According to one embodiment of the present application, L is selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms.
According to one embodiment of the present application, R is selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 5 carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 20 carbon atoms;
the R is1、R2、R3The same or different, and each is independently selected from hydrogen, deuterium, cyano, fluorine, substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.
According to one embodiment of the present application, the substituents in L are selected from deuterium, halogen, cyano, alkyl of 1 to 4 carbon atoms, aryl of 6 to 12 carbon atoms, heteroaryl of 3 to 12 carbon atoms.
According to one embodiment of the present application, the substituents in L are selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl.
R, R according to one embodiment of the present application1、R2、R3The substituents in (A) are the same or different and are each independently selected from deuterium, halogen, cyano, alkyl having 1 to 4 carbon atoms, aryl having 6 to 12 carbon atoms which may be substituted or unsubstituted with deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, heteroaryl having 3 to 12 carbon atoms, vinyl, allyl, trifluoromethyl, trimethylsilyl.
R, R according to one embodiment of the present application1、R2、R3The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, deuterium-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, allyl, naphthyl, biphenyl, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, vinyl, trifluoromethyl, trimethylsilyl.
According to another embodiment of the present application, L is selected from a single bond or from the group consisting of the groups represented by formula j-1 to formula j-14:
Figure BDA0002629645180000071
Figure BDA0002629645180000081
wherein M is2Selected from a single bond or
Figure BDA0002629645180000082
Q1～Q5And Q'1～Q’5Each independently selected from N or C (F)5) And Q is1～Q5At least one is selected from N; when Q is1～Q5Two or more of them are selected from C (F)5) When, two arbitrary F5Same or different, when Q'1～Q’4Two or more of C (F)5) When, two arbitrary F5The same or different;
Q6～Q13each independently selected from N or C (F)6) And Q is6～Q13At least one is selected from N; when Q is6～Q13Two or more of C (F)6) When, two arbitrary F6The same or different;
Q14～Q23each independently selected from N or C (F)7) And Q is14～Q23At least one is selected from N; when Q is14～Q23Two or more of C (F)7) When, two arbitrary F7The same or different;
Q24～Q32each independently selected from N or C (F)8) And Q is24～Q33At least one is selected from N; when Q is24～Q32Two or more of C (C)F8) When, two arbitrary F8The same or different.
E1～E14、F5～F8Each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, heteroaryl having 3 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, arylsilyl having 8 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, alkenyl having 2 to 6 carbon atoms, alkynyl having 2 to 6 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms, cycloalkenyl having 5 to 10 carbon atoms, heterocycloalkenyl having 4 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylamino having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 18 carbon atoms, arylamino having 6 to 18 carbon atoms, arylthio having 6 to 18 carbon atoms, phosphonoxy having 6 to 18 carbon atoms, mercapto having 2 to 10 carbon atoms, mercapto having 1 to 10 carbon atoms, mercapto, and mercapto, An alkylsulfonyl group having 6 to 18 carbon atoms, a trialkylphosphino group having 3 to 18 carbon atoms, a trialkylboron group having 3 to 18 carbon atoms, wherein when E1～E14When any one of them is independently selected from aryl groups having 6 to 20 carbon atoms, E1～E3And E14Is not an aryl group;
eris a substituent ErR is any integer of 1-14; when r is selected from 1,2, 3,4, 5, 6, 9, 13 or 14, erSelected from 1,2, 3 or 4; when r is selected from 7 or 11, erSelected from 1,2, 3,4, 5 or 6; when r is 12, erSelected from 1,2, 3,4, 5, 6 or 7; when r is selected from 8 or 10, erSelected from 1,2, 3,4, 5, 6, 7 or 8; when e isrWhen greater than 1, any two of ErThe same or different;
K3selected from O, S, Se, N (E)15)、C(E16E17)、Si(E18E19) (ii) a Wherein E is15To E19Each independently selected from: an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, and a C2 to 6 alkenyl groups, 2 to 6 alkynyl groups, 3 to 10 cycloalkyl groups, 2 to 10 heterocycloalkyl groups, 5 to 10 cycloalkenyl groups, 4 to 10 heterocycloalkenyl groups, or E16And E17Atoms that are linked to each other to be commonly bound to them form a ring; or E above18And E19Atoms that are linked to each other to be commonly bound to them form a ring; in addition, K is3In, E16And E17、E18And E19May be linked to each other so as to form a saturated or unsaturated cyclic form with the atoms to which they are linked together, or may be present independently of each other. For example, when E16And E17Cyclization E18And E19When the ring is formed, the number of carbon atoms of the ring may be 5-membered, for example
Figure BDA0002629645180000083
Or may be a 6-membered ring, e.g.
Figure BDA0002629645180000084
And may also be a 13-membered ring, e.g.
Figure BDA0002629645180000091
Of course, E16And E17Cyclization E18And E19The number of carbon atoms in the ring may be other numbers, which are not listed here, and the number of carbon atoms in the ring is not particularly limited in this application.
K4Selected from the group consisting of a single bond, O, S, Se, N (E)20)、C(E21E22)、Si(E23E24) (ii) a Wherein E is20To E24Each independently selected from: an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, a cycloalkenyl group having 5 to 10 carbon atoms, a heterocycloalkenyl group having 4 to 10 carbon atoms, or E21And E22To each other to form a ring with the atoms to which they are commonly attached, or E as described above23And E24The atoms that are linked to each other to be commonly linked to them form a ring. This application is not directed to E21And E22Number of carbon atoms in Ring formation, E23And E24The number of carbon atoms forming the ring is specifically limited. E21And E22Cyclization E23And E24Number of carbon atoms in Ring formation and E16And E17The same ring formation process is not repeated here.
Alternatively, L is selected from a single bond or from the group consisting of the groups represented by formula j-15:
Figure BDA0002629645180000092
wherein Q is33～Q42Each independently selected from N or C (F)9) And Q is33～Q42At least one is selected from N; when Q is33～Q42Two or more of C (F)9) When, two arbitrary F9The same or different;
F9each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, heteroaryl having 3 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, arylsilyl having 8 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, alkenyl having 2 to 6 carbon atoms, alkynyl having 2 to 6 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms, cycloalkenyl having 5 to 10 carbon atoms, heterocycloalkenyl having 4 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylamino having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 18 carbon atoms, arylamino having 6 to 18 carbon atoms, arylthio having 6 to 18 carbon atoms, phosphonoxy having 6 to 18 carbon atoms, mercapto having 2 to 10 carbon atoms, mercapto having 1 to 10 carbon atoms, mercapto, and mercapto, An alkylsulfonyl group having 6 to 18 carbon atoms, a trialkylphosphino group having 3 to 18 carbon atoms, and a trialkylboron group having 3 to 18 carbon atoms.
Alternatively, L is selected from a single bond or the group consisting of:
Figure BDA0002629645180000093
as a further preference, L is selected from a single bond or from the group consisting of:
Figure BDA0002629645180000101
wherein, represents is used for
Figure BDA0002629645180000102
And represents a bond for bonding to R.
According to another embodiment of the present application, L is selected from a single bond or from the group consisting of:
Figure BDA0002629645180000103
wherein, represents is used for
Figure BDA0002629645180000104
And represents a bond for bonding to R.
According to another embodiment of the present application, R is selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms or groups represented by the following chemical formula i-1 to chemical formula i-15;
the R is1、R2、R3Selected from the group consisting of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, or groups represented by the following chemical formula i-1 to chemical formula i-15:
Figure BDA0002629645180000111
wherein M is1Is selected fromA key or
Figure BDA0002629645180000112
G1～G5And G'1～G’4Each independently selected from N or C (F)1) And G is1～G5At least one is selected from N; when G is1～G5Two or more of C (F)1) When, two arbitrary F1The same or different; when G'1～G’4Two or more of C (F)1) When, two arbitrary F1The same or different;
G6～G13each independently selected from N or C (F)2) And G is6～G13At least one is selected from N; when G is6～G13Two or more of C (F)2) When, two arbitrary F2The same or different;
G14～G23each independently selected from N or C (F)3) And G is14～G23At least one is selected from N; when G is14～G23Two or more of C (F)3) When, two arbitrary F3The same or different;
G24～G33each independently selected from N or C (F)4) And G is24～G33At least one is selected from N; when G is24～G33Two or more of C (F)4) When, two arbitrary F4The same or different;
H1～H21、F1～F4each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, arylsilyl having 8 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, alkenyl having 2 to 6 carbon atoms, alkynyl having 2 to 6 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms, carbon atom-containing alkyl5-10 cycloalkenyl groups, 4-10 heterocycloalkenyl groups, 1-10 alkoxy groups, 1-10 alkylamino groups, 1-10 alkylthio groups, 6-18 aryloxy groups, 6-18 arylamine groups, 6-18 arylthio groups, 6-18 phosphonooxy groups, 6-18 alkylsulfonyl groups, 3-18 trialkylphosphino groups, and 3-18 trialkylboron groups; wherein, when H4～H20When any one of them is independently selected from aryl with 6-20 carbon atoms, H1～H3And H21Is not an aryl group;
hkis a substituent HkK is any integer of 1-21; wherein, when k is selected from 5 or 17, hkSelected from 1,2 or 3; when k is selected from 2, 7, 8, 12, 15, 16, 18 or 21, hkSelected from 1,2, 3 or 4; when k is selected from 1, 3,4, 6, 9 or 14, hkSelected from 1,2, 3,4 or 5; when k is 13, hkSelected from 1,2, 3,4, 5 or 6; when k is selected from 10 or 19, hkSelected from 1,2, 3,4, 5, 6 or 7; when k is selected from 20, hkSelected from 1,2, 3,4, 5, 6, 7 or 8; when k is 11, hkSelected from 1,2, 3,4, 5, 6, 7, 8 or 9; when h is generatedkWhen greater than 1, any two HkThe same or different;
K1selected from O, S, Se, N (H)22)、C(H23H24)、Si(H25H26) (ii) a Wherein H22～H26Each independently selected from: an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, a cycloalkenyl group having 5 to 10 carbon atoms, a heterocycloalkenyl group having 4 to 10 carbon atoms, or the above H23And H24Atoms linked to each other to form a ring together with them, or the above-mentioned H25And H26Interconnected to be commonly connected therewithThe atoms form a ring; in addition, K is1In (H)23And H24、H25And H26May be linked to each other so as to form a saturated or unsaturated cyclic form with the atoms to which they are linked together, or may be present independently of each other. For example, when H23And H24Cyclization H25And H26When the ring is formed, the number of carbon atoms of the ring may be 5-membered, for example
Figure BDA0002629645180000121
Or may be a 6-membered ring, e.g.
Figure BDA0002629645180000122
And may also be a 13-membered ring, e.g.
Figure BDA0002629645180000123
Of course, H23And H24、H25And H26The number of carbon atoms in the ring may be other numbers, which are not listed here, and the number of carbon atoms in the ring is not particularly limited in this application.
K2Selected from single bond, O, S, Se, N (H)27)、C(H28H29)、Si(H30H31) (ii) a Wherein H27～H31Each independently selected from: an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, a cycloalkenyl group having 5 to 10 carbon atoms, a heterocycloalkenyl group having 4 to 10 carbon atoms, or the above H28And H29Atoms linked to each other to form a ring together with them, or the above-mentioned H30And H31The atoms that are linked to each other to be commonly linked to them form a ring. H28And H29Cyclization H30And H31Number of carbon atoms forming ring and H23And H24The same ring formation process is not repeated here.
Alternatively, R is selected from substituted or unsubstituted alkyl with 1-5 carbon atoms or substituted or unsubstituted W;
the R is1、R2、R3Selected from hydrogen, deuterium, cyano, fluorine, substituted or unsubstituted alkyl having 1 to 5 carbon atoms, or substituted or unsubstituted W selected from the group consisting of:
Figure BDA0002629645180000124
when the W group is substituted, the substituent of W is selected from hydrogen, deuterium, fluorine, chlorine, cyano, trimethylsilyl, alkyl with 1-5 carbon atoms, halogenated alkyl with 1-4 carbon atoms, aryl with 6-12 carbon atoms, alkenyl with 2-4 carbon atoms and heteroaryl with 3-12 carbon atoms; when there are a plurality of substituents for W, the substituents may be the same or different.
Optionally, R is selected from alkyl with 1-5 carbon atoms or the group consisting of the following groups:
Figure BDA0002629645180000131
the R is1、R2、R3Selected from hydrogen, deuterium, cyano, fluorine, alkyl with 1-5 carbon atoms or the group consisting of the following groups:
Figure BDA0002629645180000132
optionally, R is selected from alkyl with 1-5 carbon atoms or the group consisting of the following groups:
Figure BDA0002629645180000133
alternatively, R is selected from methyl, ethyl, isopropyl, tert-butyl or a group consisting of:
Figure BDA0002629645180000134
Figure BDA0002629645180000141
the R is1、R2、R3Selected from hydrogen, deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl or a group consisting of:
Figure BDA0002629645180000142
optionally, the organic compound of the present application is selected from the group consisting of:
Figure BDA0002629645180000143
Figure BDA0002629645180000151
Figure BDA0002629645180000161
Figure BDA0002629645180000171
Figure BDA0002629645180000181
Figure BDA0002629645180000191
Figure BDA0002629645180000201
the following synthetic examples and examples serve to further illustrate and explain the contents of the present application.
Generally, the organic compounds of the present application can be prepared by the methods described herein. Unless otherwise specified, the meanings of the substituent symbols in the present application are the same as those of the substituent symbols in chemical formula 1. Those skilled in the art will recognize that: the chemical reactions described herein can be used to suitably prepare a number of other compounds of the present application, and other methods for preparing the organic compounds of the present application are considered to be within the scope of the present application. For example, one skilled in the art can synthesize other organic compounds of the present application by referring to or appropriately modifying the preparation methods provided herein, e.g., by using appropriate protecting groups, using other known reagents than those described herein, modifying reaction conditions, etc.
In the synthesis examples described below, the temperatures are given in degrees celsius unless otherwise stated.
The compounds of the present application were synthesized using the following methods:
Figure BDA0002629645180000202
adding 1, 2-dibromo-3-chlorobenzene (80.0g, 298.7mmol), phenylboronic acid (36.5g, 298.7mmol), tetrakis (triphenylphosphine) palladium (6.9g, 6.0mmol), potassium carbonate (103.2g, 746.7mmol) and tetrabutylammonium bromide (19.2g, 59.7mmol) into a flask, adding a mixed solvent of toluene (600mL), ethanol (150mL) and water (150mL), heating to 80 ℃ under the protection of nitrogen, keeping the temperature, stirring for 18 hours, cooling to room temperature, stopping stirring, washing the reaction liquid with water, separating an organic phase, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification by column chromatography on silica gel using dichloromethane/n-heptane as the mobile phase gave the product intermediate a-1(42.0g, 53%) as a white solid.
Intermediate b-1 and intermediate c-1 were synthesized using a similar procedure as described above, substituting reactant a in table 1 below for 1, 2-dibromo-3-chlorobenzene:
TABLE 1
Figure BDA0002629645180000211
Figure BDA0002629645180000212
Adding the intermediate a-1(42.0g, 157.9mmol) and tetrahydrofuran (300mL) into a flask, cooling to-78 ℃ under the protection of nitrogen, adding a tetrahydrofuran (2.5M) solution (95mL, 236.9mmol) of n-butyllithium dropwise under stirring, stirring while maintaining the temperature constant for 1 hour after the dropwise addition, adding a tetrahydrofuran (100mL) solution dissolved with adamantanone (19.0g, 126.3mmol) dropwise while maintaining the temperature constant for 1 hour after the dropwise addition, heating to room temperature after the 1 hour after the dropwise addition, stirring for 24 hours, adding a water (100mL) solution of hydrochloric acid (12M) (26.3mL, 315.8mmol) into the reaction solution, stirring for 1 hour, separating, washing the organic phase to neutrality with water, adding anhydrous magnesium sulfate, drying under reduced pressure to remove the solvent to obtain a crude product, purifying the crude product by silica gel column chromatography using an ethyl acetate/n-heptane system to obtain a white solid product, intermediate a-2(25.8g, 48%).
Intermediate b-2 and intermediate c-2 were synthesized using a similar procedure as described above, substituting reactant a for intermediate a-1 in table 2 below:
TABLE 2
Figure BDA0002629645180000213
Figure BDA0002629645180000214
Adding the intermediate a-2(25.8g, 76.3mmol) and glacial acetic acid (300mL) into a flask, slowly dropwise adding a concentrated sulfuric acid (98%) (0.8mL, 15.3mmol) solution in acetic acid (20mL) under the condition of nitrogen protection and normal temperature stirring, raising the temperature to 80 ℃ after dropwise addition, and stirring for 2 hours; cooling to room temperature, filtering the precipitated solid, leaching the filter cake with water and ethanol, and drying to obtain a crude product; the crude product was purified by column chromatography on silica gel using a dichloromethane/n-heptane system to give intermediate a-3(20.4g, 84%) as a white solid.
Intermediate b-3 and intermediate c-3 were synthesized using a similar procedure as described above, substituting intermediate a-2 with reactant a in table 3 below:
TABLE 3
Figure BDA0002629645180000221
Figure BDA0002629645180000222
Adding the intermediate a-3(20.4g, 63.7mmol), pinacol diboron diborate (19.4g, 76.5mmol), tris (dibenzylideneacetone) dipalladium (0.6g, 0.6mmol), 2-dicyclohexylphosphonium-2 ',4',6' -triisopropylbiphenyl (0.6g, 1.3mmol), potassium acetate (12.5g, 127.4mmol) and 1, 4-dioxane (150mL) to a flask, and stirring at 100 ℃ under nitrogen protection for 16 hours under reflux; cooling to room temperature, adding dichloromethane and water into the reaction solution, separating, washing the organic phase with water, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; the crude product was purified by column chromatography on silica gel using a dichloromethane/n-heptane system to give intermediate a-4(13.3g, 51%) as a white solid.
Intermediate b-4 and intermediate c-4 were synthesized using a similar procedure as described above, substituting reactant a for intermediate a-3 in table 4 below:
TABLE 4
Figure BDA0002629645180000223
Figure BDA0002629645180000224
Adding the intermediate a-4(13.3g, 32.3mmol), 2-nitrobromobenzene (7.1g, 35.5mmol), tetratriphenylphosphine palladium (0.7g, 0.6mmol), potassium carbonate (11.1g, 80.7mmol) and tetrabutylammonium bromide (2.1g, 6.5mmol) into a flask, adding a mixed solvent of toluene (80mL), ethanol (20mL) and water (20mL), heating to 80 ℃ under the protection of nitrogen, keeping the temperature, stirring for 24 hours, cooling to room temperature, stopping stirring, washing the reaction liquid with water, separating an organic phase, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification by column chromatography on silica gel using dichloromethane/n-heptane as mobile phase gave the product intermediate a-i (9.0g, 69%) as a white solid.
The intermediates shown in the following table were synthesized using a similar procedure using reactant a instead of intermediate a-4 and reactant B instead of 2-nitrobromobenzene in table 5 below:
TABLE 5
Figure BDA0002629645180000231
Figure BDA0002629645180000241
Figure BDA0002629645180000242
Adding the intermediate b-4(7.6g, 23.7mmol), 2-chloroaniline (3.2g, 24.9mmol), tris (dibenzylideneacetone) dipalladium (0.2g, 0.2mmol), 2-dicyclohexylphosphonium-2 ',4',6' -triisopropylbiphenyl (0.2g, 0.5mmol), sodium tert-butoxide (3.4g, 35.6mmol) and toluene (50mL) to a flask, and stirring at 105 ℃ under nitrogen protection for 4 hours under reflux; cooling to room temperature, washing the reaction solution with water, separating liquid, washing the organic phase with water, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; the crude product was purified by column chromatography on silica gel using a dichloromethane/n-heptane system to give intermediates b-iv (7.7g, 79%) as white solids.
Intermediates shown in the following table were synthesized using a similar procedure as described above using reactant a instead of intermediate B-4 and reactant B instead of 2-chloroaniline in table 6 below:
TABLE 6
Figure BDA0002629645180000243
Figure BDA0002629645180000251
Figure BDA0002629645180000252
Adding the intermediate a-i (9.0g, 22.1mmol), triphenylphosphine (14.5g, 55.3mmol) and o-dichlorobenzene (100mL) into a flask, heating to 175 ℃ under the protection of nitrogen, and stirring for 18 hours; cooling to room temperature, washing the reaction solution with water, separating liquid, washing the organic phase with water, drying with anhydrous magnesium sulfate, and removing the solvent at high temperature under reduced pressure to obtain a crude product; the crude product was purified by column chromatography on silica gel using ethyl acetate/n-heptane to yield intermediate A (7.5g, 90%) as a white solid.
Similar methods were used to synthesize the intermediates shown in the following table, substituting reactant a for intermediates a-i in table 7 below:
TABLE 7
Figure BDA0002629645180000253
Figure BDA0002629645180000261
Figure BDA0002629645180000262
Adding the intermediate b-iv (7.7g, 18.7mmol), palladium acetate (2.1g, 9.4mmol), cesium carbonate (24.4g, 74.9mmol), tricyclohexylphosphine tetrafluoroborate (6.9g, 18.7mmol) and dimethylacetamide (70mL) into a flask, heating to 160 ℃ under the protection of nitrogen, stirring for 12 hours, cooling to room temperature, adding dichloromethane (300mL) into the reaction liquid, washing with a large amount of water, drying the obtained organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; the crude product was purified by column chromatography on silica gel using a dichloromethane/n-heptane system to yield intermediate K (6.0g, 85%) as a white solid.
Similar methods were used to synthesize the intermediates shown in the following table, using reactant a in the following table 8 instead of intermediates b-iv:
TABLE 8
Figure BDA0002629645180000271
Figure BDA0002629645180000281
Figure BDA0002629645180000282
Adding the intermediate A (7.5g, 20.2mmol), 4-bromobiphenyl (4.9g, 21.0mmol), cuprous iodide (0.8g, 4.0mmol), potassium carbonate (6.1g, 43.9mmol), 1, 10-phenanthroline (1.4g, 8.0mmol), 18-crown-6-ether (0.5g, 2.0mmol) and dimethylformamide (50mL) into a flask, heating to 145 ℃ under the protection of nitrogen, stirring for 12 hours, cooling to room temperature, adding dichloromethane (100mL) and water into a reaction solution, separating, washing an organic phase with water, adding anhydrous magnesium sulfate, drying, and removing a solvent under reduced pressure to obtain a crude product; the crude product was purified by silica gel column chromatography using a methylene chloride/n-heptane system and then purified by recrystallization using a toluene/n-heptane system to give the product compound 1(5.5g, 52%) as a white solid.
In table 9 below, the compounds shown in the following table were synthesized using a similar procedure, substituting reactant a for intermediate a and reactant B for 4-bromobiphenyl:
TABLE 9
Figure BDA0002629645180000283
Figure BDA0002629645180000291
Figure BDA0002629645180000301
Figure BDA0002629645180000302
Adding the intermediate K (6.0g, 16.0mmol), 2-chloro-4-phenylbenzo [ h ] quinazoline (4.9g, 16.8mmol), 4-dimethylaminopyridine (1.0g, 8.0mmol), cesium carbonate (5.2g, 16.0mmol) and dimethyl sulfoxide (80mL) into a round-bottom flask, stirring and heating to 100 ℃ under the protection of nitrogen, reacting for 16 hours, cooling to room temperature after the reaction is finished, filtering, leaching a filter cake with water and ethanol, and drying to obtain a crude product; the crude product was purified by recrystallization from toluene to give compound 20 as a yellow solid (5.1g, 51%).
In the following Table 10, reactant A replaces intermediate K and reactant B replaces 2-chloro-4-phenylbenzo [ h ] quinazoline, and similar methods were used to synthesize the compounds shown in the following Table:
watch 10
Figure BDA0002629645180000303
Figure BDA0002629645180000311
Mass spectrometry analysis was performed on the above compounds, and the data are shown in table 11 below:
TABLE 11
Figure BDA0002629645180000312
Figure BDA0002629645180000321
Nuclear magnetic resonance hydrogen spectral data of compound 28:
1H NMR(CD2Cl2400MHz) 9.03(d,1H),8.39(d,1H),8.32(br,4H),8.20(d,1H),8.12(d,1H),8.03(d,1H),7.61(t,1H),7.55(t,2H),7.49(t,1H),7.43(t,4H),7.03(t,1H),6.97(d,1H),6.90(t,1H),3.14(d,4H),2.31(d,2H),2.10(s,2H),1.96(t,4H),1.87(s,2H) the spectrogram is shown in FIG. 3.
Nuclear magnetic resonance hydrogen spectroscopy data for compound 130:
1H NMR(CD2Cl2,400MHz):9.76(s,1H),9.00(d,1H),8.76(d,4H),8.44(s,1H),8.18-8.15(m,2H),7.96(d,1H),7.68(t,2H),7.63-7.58(m,5H),7.47-7.42(m,2H),7.31(t,1H),3.21(d,2H),2.99(d,2H),2.21(s,1H),1.96-1.94(m,3H),1.83-1.79(m,4H),1.86(s,2H).
nuclear magnetic resonance hydrogen spectral data of compound 132:
1H NMR(CD2Cl2,400MHz):9.64(s,1H),9.21(d,1H),8.84(d,4H),8.76(s,1H),8.19-8.16(m,2H),8.01(d,1H),7.73-7.67(m,6H),7.61(t,1H),7.48-7.45(m,2H),7.35(t,1H),3.14(d,2H),3.00(d,2H),2.37(s,1H),2.26(s,1H),2.08(s,2H),1.93-1.86(m,4H),1.68(s,2H).
the application also provides an electronic component for realizing the electro-optical conversion. The electronic element comprises an anode and a cathode which are oppositely arranged, and a functional layer arranged between the anode and the cathode; the functional layer comprises an organic compound of the present application.
The electronic element of the present application may be, for example, an organic electroluminescent device or a photoelectric conversion device.
According to one embodiment, the electronic component is an organic electroluminescent device. The organic electroluminescent device can be, for example, a red organic electroluminescent device or a green organic electroluminescent device.
As shown in fig. 1, the organic electroluminescent device includes an anode 100 and a cathode 200 oppositely disposed, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 comprises an organic compound as provided herein.
Alternatively, the functional layer 300 includes a light emitting layer 330, the light emitting layer 330 including an organic compound provided herein.
In one embodiment of the present application, the organic electroluminescent device may include an anode 100, a hole injection layer 310, a hole transport layer 321, an electron blocking layer 322, an organic electroluminescent layer 330 as an energy conversion layer, an electron transport layer 350, an electron injection layer 360, and a cathode 200, which are sequentially stacked. The organic compound provided by the application can be applied to the light-emitting layer 330 of the organic electroluminescent device, and the service life of the organic electroluminescent device can be effectively improved.
Optionally, the anode 100 comprises an anode material, preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metals and oxides, e.g. ZnO: Al or SnO2Sb; or a conductive polymer such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode including Indium Tin Oxide (ITO) as an anode is included.
Alternatively, the hole transport layer 321 may include one or more hole transport materials, and the hole transport material may be selected from carbazole multimer, carbazole-linked triarylamine-based compound, or other types of compounds, which are not specifically limited herein. For example, the hole transport layer 321 may comprise compounds HT-01 or HT-03.
Optionally, the electron blocking layer 322 includes one or more electron blocking materials, and the electron blocking materials may be selected from carbazole multimers or other types of compounds, which are not particularly limited in this application. For example, the electron blocking layer 322 may comprise compounds HT-02, HT-04, or HT-05.
Alternatively, the organic electroluminescent layer 330 is composed of a host material and a guest material, and the compound of the present application may be used as the host material. The holes injected into the organic electroluminescent layer 330 and the electrons injected into the organic luminescent layer 330 may be recombined in the organic luminescent layer 330 to form excitons, which transfer energy to the host material, which transfers energy to the guest material, thereby enabling the guest material to emit light.
The guest material of the organic electroluminescent layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which is not particularly limited in the present application. In one embodiment of the present application, the guest material of the organic light emitting layer 330 may be Ir (piq)2(acac) or Ir (ppy)3。
Optionally, the cathode 200 comprises a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multilayer material such as LiF/Al, Liq/Al, LiO2Al, LiF/Ca, LiF/Al and BaF2But not limited thereto,/Ca. Preferably, a metal electrode comprising silver and magnesium is included as a cathode.
Optionally, as shown in fig. 1, a hole injection layer 310 may be further disposed between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, which are not limited in this application. In one embodiment of the present application, the hole injection layer 310 may be composed of F4-TCNQ.
Optionally, as shown in fig. 1, an electron injection layer 360 may be further disposed between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic material. In one embodiment of the present application, the electron injection layer 360 may include ytterbium (Yb).
Optionally, a hole blocking layer 340 may be further disposed between the organic electroluminescent layer 330 and the electron transport layer 350.
The embodiment of the application also provides an electronic device, which comprises any one of the electronic elements described in the electronic element embodiment. Since the electronic device has any one of the electronic elements described in the above embodiments of the electronic element, the electronic device has the same beneficial effects, and the details of the electronic device are not repeated herein.
For example, as shown in fig. 2, the present application provides an electronic device 400, wherein the electronic device 400 includes any one of the organic electroluminescent devices described in the above organic electroluminescent device embodiments. The electronic device 400 may be a display device, a lighting device, an optical communication device, or other types of electronic devices, and may include, but is not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like. Since the electronic device 400 has any one of the organic electroluminescent devices described in the above embodiments of the organic electroluminescent device, the same advantages are obtained, and details are not repeated herein.
Preparation and performance evaluation of organic electroluminescent device
Example 1: green organic electroluminescent device
The anode was prepared by the following procedure: will have a thickness of
Figure BDA0002629645180000331
The ITO substrate (manufactured by Corning) of (1) was cut into a size of 40mm (length) × 40mm (width) × 0.7mm (thickness), prepared into an experimental substrate having a cathode, an anode and an insulating layer pattern using a photolithography process, using ultraviolet ozone and O2:N2The plasma was surface treated to increase the work function of the anode (experimental substrate) and to remove scum.
F4-TCNQ was vacuum-deposited on an experimental substrate (anode) to a thickness of
Figure BDA0002629645180000342
And HT-01 is vapor-deposited on the hole injection layer to form a Hole Injection Layer (HIL) having a thickness of
Figure BDA0002629645180000343
The first hole transport layer of (1).
Vacuum evaporating HT-02 on the first hole transport layer to a thickness of
Figure BDA0002629645180000344
The second hole transport layer of (1).
On the second hole transport layer, compound 1: GHn 1: ir (ppy)3In a ratio of 50%: 45%: 5% of the total amount of the components are co-evaporated to form a film with a thickness of
Figure BDA0002629645180000345
Green emitting layer (EML).
ET-01 and LiQ are mixed according to the weight ratio of 1:1 and evaporated to form
Figure BDA0002629645180000346
A thick Electron Transport Layer (ETL), and depositing LiQ on the electron transport layer to form a layer with a thickness of
Figure BDA0002629645180000347
And then magnesium (Mg) and silver (Ag) are mixed in a ratio of 1: 9 is vacuum-evaporated on the electron injection layer to a thickness of
Figure BDA0002629645180000348
The cathode of (1).
The thickness of the vapor deposition on the cathode is set to
Figure BDA0002629645180000349
Forming an organic capping layer (CPL), thereby completing an organic hairAnd (5) manufacturing the optical device.
Example 2 to example 8
An organic electroluminescent device was produced in the same manner as in example 1, except that the mixed components shown in table 13 below were substituted for the mixed components in example 1 in forming the light-emitting layer.
Comparative example 1 to comparative example 3
Organic electroluminescent devices were produced in the same manner as in example 1, except that the mixed components shown in table 12 below were substituted for the mixed components in example 1 in forming the light-emitting layer.
The material structures used in the above examples and comparative examples are shown in table 12 below:
TABLE 12
Figure BDA0002629645180000341
Figure BDA0002629645180000351
For the organic electroluminescent device prepared as above, at 20mA/cm2The device performance was analyzed under the conditions shown in table 13 below:
watch 13
Figure BDA0002629645180000352
Referring to table 13 above, it can be seen that the compound of the present application used as a green light emitting layer mixed host material in examples 1-8 has a device lifetime prolonged by at least 42% compared to that of comparative examples 1-3 under the premise of similar driving voltage and light emitting efficiency.
Therefore, when the novel compound is used for preparing a green organic electroluminescent device, the service life of the organic electroluminescent device can be effectively prolonged, and the luminous efficiency can be improved to a certain extent.
Example 9: red organic electroluminescent device
The anode was prepared by the following procedure: will have a thickness of
Figure BDA0002629645180000362
The ITO substrate (manufactured by Corning) of (1) was cut into a size of 40mm (length) × 40mm (width) × 0.7mm (thickness), prepared into an experimental substrate having a cathode, an anode and an insulating layer pattern using a photolithography process, using ultraviolet ozone and O2:N2The plasma was surface treated to increase the work function of the anode (experimental substrate) and to remove scum.
F4-TCNQ was vacuum-deposited on an experimental substrate (anode) to a thickness of
Figure BDA0002629645180000363
And a Hole Injection Layer (HIL) formed by evaporating HT-03 to a thickness of
Figure BDA0002629645180000364
The first hole transport layer of (1).
Vacuum evaporating HT-04 on the first hole transport layer to form a layer with a thickness of
Figure BDA0002629645180000365
The second hole transport layer of (1).
On the second hole transport layer, compound 40: ir (piq)2(acac) at 95%: 5% of the total amount of the components are co-evaporated to form a film with a thickness of
Figure BDA0002629645180000366
Red emitting layer (EML).
ET-02 and LiQ were mixed at a weight ratio of 1:1 and vapor-deposited to form
Figure BDA0002629645180000368
A thick Electron Transport Layer (ETL), and depositing LiQ on the electron transport layer to form a layer with a thickness of
Figure BDA0002629645180000367
And then an Electron Injection Layer (EIL), andmixing magnesium (Mg) and silver (Ag) in a ratio of 1: 9 is vacuum-evaporated on the electron injection layer to a thickness of
Figure BDA0002629645180000369
The cathode of (1).
The thickness of the vapor deposition on the cathode is set to
Figure BDA00026296451800003610
Forming an organic capping layer (CPL), thereby completing the fabrication of the organic light emitting device.
Example 10-example 17
An organic electroluminescent device was produced in the same manner as in example 9, except that in the formation of the light-emitting layer, compounds shown in table 15 below were used instead of the compound 40.
Comparative example 4
An organic electroluminescent device was fabricated by the same method as in example 9, except that BAlq was used instead of the compound 40 in forming the light-emitting layer.
Comparative example 5
An organic electroluminescent device was produced in the same manner as in example 9, except that the compound D was used instead of the compound 40 in forming the light-emitting layer.
The material structures used in the above examples and comparative examples are shown in table 14 below:
TABLE 14
Figure BDA0002629645180000361
Figure BDA0002629645180000371
For the organic electroluminescent device prepared as above, at 20mA/cm2The device performance was analyzed under the conditions shown in table 15 below:
watch 15
Figure BDA0002629645180000372
Referring to table 15 above, the compounds of the present application used as host materials of red light emitting layers in examples 9-17 showed a minimum decrease in device driving voltage of 17% and a minimum increase in light emitting efficiency of 15% as compared to comparative example 4; compared with comparative example 5, the luminous efficiency is improved by 15% at least, and the service life is improved to a certain extent.
Therefore, when the novel compound is used for preparing a red organic electroluminescent device, the efficiency of the organic electroluminescent device can be effectively improved, and the service life of the organic electroluminescent device is also improved.
Example 18: red organic electroluminescent device
The anode was prepared by the following procedure: will have a thickness of
Figure BDA0002629645180000373
The ITO substrate (manufactured by Corning) of (1) was cut into a size of 40mm (length) × 40mm (width) × 0.7mm (thickness), prepared into an experimental substrate having a cathode, an anode and an insulating layer pattern using a photolithography process, using ultraviolet ozone and O2:N2The plasma was surface treated to increase the work function of the anode (experimental substrate) and to remove scum.
F4-TCNQ was vacuum-deposited on an experimental substrate (anode) to a thickness of
Figure BDA0002629645180000374
And a Hole Injection Layer (HIL) formed by evaporating HT-03 to a thickness of
Figure BDA0002629645180000375
The first hole transport layer of (1).
Vacuum evaporating HT-05 on the first hole transport layer to a thickness of
Figure BDA0002629645180000376
The second hole transport layer of (1).
On the second hole transport layer, compound 52：RHn1：Ir(piq)2(acac) at 50%: 45%: 5% of the total amount of the components are co-evaporated to form a film with a thickness of
Figure BDA0002629645180000377
Red emitting layer (EML).
ET-03 and LiQ are mixed according to the weight ratio of 2:1 and evaporated to form
Figure BDA0002629645180000379
A thick Electron Transport Layer (ETL), and depositing LiQ on the electron transport layer to form a layer with a thickness of
Figure BDA0002629645180000378
And then magnesium (Mg) and silver (Ag) are mixed in a ratio of 1: 9 is vacuum-evaporated on the electron injection layer to a thickness of
Figure BDA00026296451800003710
The cathode of (1).
The thickness of the vapor deposition on the cathode is set to
Figure BDA0002629645180000382
Forming an organic capping layer (CPL), thereby completing the fabrication of the organic light emitting device.
Example 19 example 23
An organic electroluminescent device was produced in the same manner as in example 18, except that the mixed components shown in table 17 below were used instead of the mixed components in example 18 in forming the light-emitting layer.
Comparative example 6 to comparative example 7
An organic electroluminescent device was produced in the same manner as in example 18, except that the mixed components shown in table 16 below were used instead of the mixed components in example 18 in forming the light-emitting layer.
The material structures used in the above examples and comparative examples are shown in table 16 below:
TABLE 16
Figure BDA0002629645180000381
For the organic electroluminescent device prepared as above, at 20mA/cm2The device performance was analyzed under the conditions shown in table 17 below:
TABLE 17
Figure BDA0002629645180000391
Referring to table 17 above, it can be seen that the compounds of examples 18-23 used as host materials for red light-emitting layer mixture have 15% longer lifetime compared to comparative examples 6 and 7 with similar driving voltage and light-emitting efficiency.
Therefore, when the novel compound is used for preparing a mixed host type red organic electroluminescent device, the service life of the organic electroluminescent device can be effectively prolonged.

Claims (11)

1. An organic compound having a structural formula shown in chemical formula 1 and chemical formula 2:
Figure FDA0003206092260000011
wherein two of chemical formula 2 are combined with any adjacent two of four of chemical formula 1 to form a fused ring;
ring B is a benzene ring or a naphthalene ring;
l is selected from a single bond or from the group consisting of:
Figure FDA0003206092260000012
r is selected from substituted or unsubstituted W, said unsubstituted W is selected from the group consisting of;
Figure FDA0003206092260000013
when the W group is substituted, the substituent of W is selected from hydrogen, deuterium, fluorine, chlorine, cyano, alkyl with 1-5 carbon atoms, halogenated alkyl with 1-4 carbon atoms, aryl with 6-12 carbon atoms and heteroaryl with 3-12 carbon atoms; when there are a plurality of substituents for W, the substituents may be the same or different; or
R is selected from
Figure FDA0003206092260000014
R1、R2、R3Selected from hydrogen, deuterium and alkyl with 1-5 carbon atoms;
ntis a substituent RtT is any integer of 1-3; when t is 1, ntSelected from 1,2, 3 or 4; when t is selected from 2, ntIs selected from 1 or 2; when t is 3, ntSelected from 1,2, 3,4, 5, 6; when n istWhen greater than 1, any two RtThe same or different.
2. The organic compound according to claim 1, wherein the chemical formula 2 is any one of chemical formulas 2-1, 2-2, 2-3, and 2-4:
Figure FDA0003206092260000021
3. the organic compound of claim 1, wherein L is selected from a single bond or from the group consisting of:
Figure FDA0003206092260000022
wherein, represents is used for
Figure FDA0003206092260000023
And represents a bond for bonding to R.
4. The organic compound of claim 1, wherein L is selected from a single bond or from the group consisting of:
Figure FDA0003206092260000031
wherein, represents is used for
Figure FDA0003206092260000032
And represents a bond for bonding to R.
5. The organic compound of claim 1, wherein R is selected from the group consisting of:
Figure FDA0003206092260000033
6. the organic compound of claim 1, wherein R is selected from the group consisting of:
Figure FDA0003206092260000034
the R is1、R2、R3Selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl.
7. The organic compound of claim 1, wherein the organic compound is selected from the group consisting of:
Figure FDA0003206092260000041
Figure FDA0003206092260000051
Figure FDA0003206092260000061
Figure FDA0003206092260000071
Figure FDA0003206092260000081
Figure FDA0003206092260000091
8. an electronic component comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode;
the functional layer comprises the organic compound according to any one of claims 1 to 7.
9. The electronic element according to claim 8, wherein the functional layer comprises a light-emitting layer comprising the organic compound according to any one of claims 1 to 7.
10. The electronic component according to claim 9, wherein the electronic component is an organic electroluminescent device.
11. An electronic device, characterized in that it comprises an electronic component according to any one of claims 8-10.
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